General Information of MET (ID: META00558)
Name 4-Androstenediol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3b,17b)-Androst-4-ene-3,17-diol; 3b,17b-Dihydroxy-4-androstene; 4-Androstene-3b,17b-diol; 4-Androstenediol; Androst-4-en-3b,17b-diol; Androst-4-ene-3beta,17beta-diol; D4-Androstene-3b,17b-diol
Source Endogenous;Sterol lipids;Food;Drug
Structure Type   Androstane steroids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Steroids and steroid derivatives
Androstane steroids
PubChem CID
136297
HMDB ID
HMDB0005849
Formula
C19H30O2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=136297"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C14210
DrugBank ID
DB01526
ChEBI ID
34386
FooDB ID
FDB023781
ChemSpider ID
120071
Physicochemical Properties Molecular Weight 290.4 Topological Polar Surface Area 40.5
XlogP 3.4 Complexity 470
Heavy Atom Count 21 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals, and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-androstenediol taken by mouth is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change 4-Androstenediol concentration: increase (FC = 2.13)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the increase of 4-androstenediol levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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